Fiona Apple: Criminal
Fiona Apple’s “Criminal,” to this day, remains one of music’s most controversial videos. But what’s interesting is that unlike many of the other songs on this list that relied on overtly uncomfortable messaging, Fiona’s was much more subtle. The video, with Fiona as its young leading lady, featured what many believed to be a kiddie Adult Videos-esque vibe. Needless to say, that didn’t exactly plop this video in most people’s good graces.